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Utilizing terpene derivatives in the synthesis of annulated terpene-imidazoles with application in the nitroaldol reaction
Authors: Kulhánek Jiří | Bureš Filip | Šimon Petr | Schweizer Bernd
Year: 2008
Type of publication: článek v odborném periodiku
Name of source: Tetrahedron Asymmetry
Publisher name: Elsevier Science BV
Place: Amsterdam
Page from-to: 2462-2469
Titles:
Language Name Abstract Keywords
cze Využití terpenových derivátů v syntéze terpen-imidazolů s aplikací v nitroaldolové reakci Dvě třídy derivátů terpenů (diketony a monoximy) byly kondenzovány na deriváty imidazolu s využitím dvou metod. Metoda A zahrnuje kondenzaci diketonů s aldehydy, metoda B pak reakci monoximů s aminy. Mechanismus metody je rovněž diskutován. Celkem bylo syntetizováno a charakterizováno 11 nových derivátů imidazolu. Dva intermediáty/vedlejší produkty byly rovněž charakterizovány pomoci X-ray analýzy. Syntetizované ligandy byly aplikovány v asymetrické Henryho reakci, kdy bylo dosaženo reakčních časů 24-72 h a enantioselektivit do 32%. imidazol; terepny; asymetrická katalýza
eng Utilizing terpene derivatives in the synthesis of annulated terpene-imidazoles with application in the nitroaldol reaction Two classes of terpene derivatives (diketones and monoximes) were condensed into annulated terpeneimidazoles using two general methods. Method A, involving the condensation of terpene diketones and aldehydes, gave lower yields than Method B, which employed terpene monoximes and amines. The mechanism of Method B is discussed. Using both methods, overall 11 new imidazole ligands were synthesized and fully characterized. The molecular structures of the side product 16 and intermediate 4b were also characterized by X-ray analysis. Regarding 1a, N-methylation and subsequent ortho-lithiation and quenching with diphenylphosphinechloride were proven. The synthesized ligands were tested in the Henry reaction providing reaction times 24?72 h and enantioselectivities up to 32% especially for the pyridine 2-substituted ligands 1c, 2c, 3b and N,P-ligand 17. imidazole; terpenes; asymmetric catalysis

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